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Synthesis of a Tetracyclo [4.4.0.0 2,4 .0 3,8 ]decanone via Intramolecular Reductive Coupling
Author(s) -
Margaretha Paul,
Tissot Paul
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650629
Subject(s) - chemistry , intramolecular force , cyclopropane , yield (engineering) , ring (chemistry) , cyclic voltammetry , electron transfer , aldol reaction , stereochemistry , medicinal chemistry , photochemistry , electrochemistry , organic chemistry , catalysis , electrode , materials science , metallurgy
The reduction of cis ‐4 a‐methyl‐1,2,4a,7,8,8 a‐hexahydronaphthalene‐2,7‐dione ( 1 ) was studied by cyclic voltammetry and product analysis. On a preparative scale, 6‐hydroxy‐3‐methyltetracyclo[4.4.0.0 2,4 .0 3,8 ]decan‐10‐one ( 2 ) was obtained in 22% yield via an intramolecular hydrodimerization/aldol reaction sequence. The CV. results (Hg, DMF) suggest that the cyclopropane ring is formed after the first electron transfer by coupling of the anion radical with the second C. C‐double bond.